1-[benzyl(methyl)amino]-3-phenoxypropan-2-ol | 80448-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[benzyl(methyl)amino]-3-phenoxypropan-2-ol
• 英文别名: 1-(benzylmethylamino)-3-phenoxypropan-2-ol
• CAS: 80448-18-6
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: ISWDYTOQZVLOCR-UHFFFAOYSA-N

物化性质

• 沸点：
  422.9±35.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-[benzyl(methyl)amino]-3-phenoxypropan-2-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以98%的产率得到1-甲基氨基-3-苯氧基-2-丙醇
  参考文献：
  名称：

  Synthesis of aryloxypropanolamines via a palladium-promoted oxyamination

  摘要：

  DOI：

  10.1021/jo00345a046
• 作为产物：
  描述：

  烯丙基苯基醚 在 lead(IV) acetate 、 氢氧化钾 、 二(氰基苯)二氯化钯 、 silver(I) acetate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 1-[benzyl(methyl)amino]-3-phenoxypropan-2-ol
  参考文献：
  名称：

  Synthesis of aryloxypropanolamines via a palladium-promoted oxyamination

  摘要：

  DOI：

  10.1021/jo00345a046

文献信息

• Phenalenyl in a Different Role: Catalytic Activation through the Nonbonding Molecular Orbital
  作者：Sudipta Raha Roy、A. Nijamudheen、Anand Pariyar、Anup Ghosh、Pavan K. Vardhanapu、Prasun K. Mandal、Ayan Datta、Swadhin K. Mandal

  DOI：10.1021/cs5010695

  日期：2014.12.5

  We have demonstrated that the nonbonding molecular orbital (NBMO) of the phenalenyl (PLY) cation can be used as a Lewis acid catalyst for different organic transformations. Detailed computational and spectroscopic studies for the aminolysis reaction of epoxide reveal that this catalysis works through a different mechanism, and the phenalenyl cation activates the amine moiety using its empty NBMO, which triggers the epoxide ring-opening reaction. It has been shown that the energy of the NBMO of PLY cation plays a key role in modulating the catalytic activity. This study establishes that the cationic state of phenalenyl unit is useful not only for construction of the spin memory device by external spin injection using its NBMO, but in addition, the same NBMO can act as an organic Lewis acceptor unit to influence the catalytic outcome of a homogeneous reaction.
• Microwave-Assisted Ring Opening of Epoxides:  A General Route to the Synthesis of 1-Aminopropan-2-ols with Anti Malaria Parasite Activities
  作者：Aélig Robin、Fraser Brown、Noemí Bahamontes-Rosa、Binghua Wu、Eric Beitz、Jürgen F. J. Kun、Sabine L. Flitsch

  DOI：10.1021/jm070553l

  日期：2007.8.1

  A series of 1-aminopropan-2-ols were synthesized and evaluated against two strains of malaria, Plasmodium falciparum FCR3 (chloroquine-resistant) and 3D7 (chloroquine-sensitive). Microwave-assisted ring opening of epoxides (aryl and alkyl glycidyl ethers, glycidol, epichlorohydrin) with various amines without catalysts generated the desired library of beta-amino alcohols rapidly and efficiently. Most of the compounds showed micromolar potency against malaria, with seven of them having IC50 values between 1 and 10 mu M against both Plasmodium falciparum strains.
• BAECKVALL, J. -E.;BYSTROEM, S. E., J. ORG. CHEM., 1982, 47, N 6, 1126-1128
  作者：BAECKVALL, J. -E.、BYSTROEM, S. E.

  DOI：——

  日期：——
• ERHARDT, P. W., SYNTH. COMMUN., 1983, 13, N 2, 103-113
  作者：ERHARDT, P. W.

  DOI：——

  日期：——
• Synthesis of aryloxypropanolamines via a palladium-promoted oxyamination
  作者：Jan E. Baeckvall、Styrbjoern E. Bystroem

  DOI：10.1021/jo00345a046

  日期：1982.3